# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xray_0117_1
_audit_block_doi                 10.5517/ccdc.csd.cc2bm95g
_database_code_depnum_ccdc_archive 'CCDC 2163495'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202202434 2022
loop_
_audit_author_name
_audit_author_address
xiayan
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2022-03-31 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_audit_creation_date             2019-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        OH-SOpAD
_chemical_formula_moiety         'C27 H23 N O3 S'
_chemical_formula_sum            'C27 H23 N O3 S'
_chemical_formula_weight         441.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1193(3)
_cell_length_b                   17.2395(7)
_cell_length_c                   15.7214(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.828(3)
_cell_angle_gamma                90
_cell_volume                     2145.65(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2634
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.3720
_cell_measurement_theta_min      3.5560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7484
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.471
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -59.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00    7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   85.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000   90.0000 134
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0531679000
_diffrn_orient_matrix_UB_12      0.0269007000
_diffrn_orient_matrix_UB_13      -0.0272390000
_diffrn_orient_matrix_UB_21      -0.0669986000
_diffrn_orient_matrix_UB_22      -0.0273100000
_diffrn_orient_matrix_UB_23      -0.0068448000
_diffrn_orient_matrix_UB_31      -0.0268025000
_diffrn_orient_matrix_UB_32      0.0149044000
_diffrn_orient_matrix_UB_33      0.0367712000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3467
_reflns_number_total             4211
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18405(5) 0.18402(3) 0.93502(3) 0.02388(14) Uani 1 1 d . . . . .
O1 O 0.1543(2) 0.07393(9) 1.08582(9) 0.0475(4) Uani 1 1 d . . . . .
H1 H 0.107351 0.115489 1.071240 0.071 Uiso 1 1 calc GR . . . .
O2 O 0.05621(16) 0.20153(8) 0.98314(9) 0.0327(3) Uani 1 1 d . . . . .
O3 O 0.15593(17) 0.20610(8) 0.84501(8) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.81532(17) 0.34345(8) 1.11666(9) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.9543(2) 0.30472(10) 1.16846(11) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.9447(2) 0.22574(10) 1.18870(12) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.846162 0.198007 1.166895 0.030 Uiso 1 1 calc R . . . .
C3 C 1.0825(2) 0.18923(11) 1.24119(12) 0.0294(4) Uani 1 1 d . . . . .
H3 H 1.077019 0.136583 1.253152 0.035 Uiso 1 1 calc R . . . .
C4 C 1.2279(2) 0.23037(12) 1.27595(12) 0.0304(5) Uani 1 1 d . . . . .
H4 H 1.318442 0.206167 1.313126 0.037 Uiso 1 1 calc R . . . .
C5 C 1.2376(2) 0.30800(12) 1.25486(11) 0.0261(4) Uani 1 1 d . . . . .
H5 H 1.335244 0.335721 1.278646 0.031 Uiso 1 1 calc R . . . .
C6 C 1.1044(2) 0.34548(10) 1.19883(11) 0.0201(4) Uani 1 1 d . . . . .
C7 C 1.1200(2) 0.42631(10) 1.16186(11) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.9516(2) 0.46748(10) 1.15504(11) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.9368(2) 0.54703(10) 1.16874(12) 0.0285(4) Uani 1 1 d . . . . .
H9 H 1.033812 0.575783 1.190706 0.034 Uiso 1 1 calc R . . . .
C10 C 0.7820(3) 0.58420(10) 1.15058(12) 0.0324(5) Uani 1 1 d . . . . .
H10 H 0.775022 0.637114 1.160713 0.039 Uiso 1 1 calc R . . . .
C11 C 0.6382(2) 0.54174(11) 1.11721(13) 0.0303(4) Uani 1 1 d . . . . .
H11 H 0.534054 0.566606 1.102835 0.036 Uiso 1 1 calc R . . . .
C12 C 0.6473(2) 0.46259(10) 1.10495(12) 0.0245(4) Uani 1 1 d . . . . .
H12 H 0.549420 0.434414 1.083000 0.029 Uiso 1 1 calc R . . . .
C13 C 0.8029(2) 0.42502(9) 1.12543(11) 0.0195(4) Uani 1 1 d . . . . .
C14 C 1.2686(2) 0.47248(12) 1.21410(13) 0.0355(5) Uani 1 1 d . . . . .
H14A H 1.251478 0.481891 1.271704 0.053 Uiso 1 1 calc GR . . . .
H14B H 1.276921 0.521086 1.185560 0.053 Uiso 1 1 calc GR . . . .
H14C H 1.370987 0.443527 1.217940 0.053 Uiso 1 1 calc GR . . . .
C15 C 1.1459(2) 0.41635(11) 1.06775(11) 0.0265(4) Uani 1 1 d . . . . .
H15A H 1.250224 0.389527 1.069425 0.040 Uiso 1 1 calc GR . . . .
H15B H 1.149690 0.466446 1.041585 0.040 Uiso 1 1 calc GR . . . .
H15C H 1.053972 0.386898 1.033935 0.040 Uiso 1 1 calc GR . . . .
C16 C 0.6668(2) 0.30128(9) 1.07543(11) 0.0190(4) Uani 1 1 d . . . . .
C17 C 0.5501(2) 0.27694(10) 1.12239(11) 0.0240(4) Uani 1 1 d . . . . .
H17 H 0.570569 0.285289 1.182259 0.029 Uiso 1 1 calc R . . . .
C18 C 0.4028(2) 0.24013(10) 1.07971(11) 0.0237(4) Uani 1 1 d . . . . .
H18 H 0.323981 0.223754 1.110675 0.028 Uiso 1 1 calc R . . . .
C19 C 0.3744(2) 0.22803(9) 0.99046(11) 0.0195(4) Uani 1 1 d . . . . .
C20 C 0.4926(2) 0.25043(10) 0.94362(11) 0.0246(4) Uani 1 1 d . . . . .
H20 H 0.473404 0.240918 0.883995 0.030 Uiso 1 1 calc R . . . .
C21 C 0.6391(2) 0.28702(10) 0.98647(11) 0.0239(4) Uani 1 1 d . . . . .
H21 H 0.719248 0.302097 0.955673 0.029 Uiso 1 1 calc R . . . .
C22 C 0.2235(2) 0.08401(10) 0.94347(11) 0.0243(4) Uani 1 1 d . . . . .
C23 C 0.2064(3) 0.04264(11) 1.01721(12) 0.0310(4) Uani 1 1 d . . . . .
C24 C 0.2492(3) -0.03569(12) 1.02254(14) 0.0426(5) Uani 1 1 d . . . . .
H24 H 0.239222 -0.064228 1.071349 0.051 Uiso 1 1 calc R . . . .
C25 C 0.3057(3) -0.07092(12) 0.95655(15) 0.0456(6) Uani 1 1 d . . . . .
H25 H 0.335072 -0.123131 0.961407 0.055 Uiso 1 1 calc R . . . .
C26 C 0.3199(3) -0.03049(14) 0.88298(16) 0.0482(6) Uani 1 1 d . . . . .
H26 H 0.356907 -0.055469 0.838225 0.058 Uiso 1 1 calc R . . . .
C27 C 0.2790(3) 0.04706(13) 0.87601(13) 0.0377(5) Uani 1 1 d . . . . .
H27 H 0.288336 0.074732 0.826518 0.045 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4455(13) . ?
S1 O3 1.4339(13) . ?
S1 C19 1.7679(17) . ?
S1 C22 1.7533(18) . ?
O1 H1 0.8200 . ?
O1 C23 1.355(2) . ?
N1 C1 1.405(2) . ?
N1 C13 1.419(2) . ?
N1 C16 1.434(2) . ?
C1 C2 1.404(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(2) . ?
C6 C7 1.526(2) . ?
C7 C8 1.523(2) . ?
C7 C14 1.525(2) . ?
C7 C15 1.550(2) . ?
C8 C9 1.397(2) . ?
C8 C13 1.400(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.389(2) . ?
C16 C21 1.388(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(2) . ?
C19 C20 1.388(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.394(3) . ?
C22 C27 1.395(2) . ?
C23 C24 1.392(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.366(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.377(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.376(3) . ?
C27 H27 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 C19 107.64(8) . . ?
O2 S1 C22 107.82(8) . . ?
O3 S1 O2 119.05(9) . . ?
O3 S1 C19 107.63(8) . . ?
O3 S1 C22 108.80(9) . . ?
C22 S1 C19 105.05(8) . . ?
C23 O1 H1 109.5 . . ?
C1 N1 C13 118.67(14) . . ?
C1 N1 C16 120.51(13) . . ?
C13 N1 C16 118.42(14) . . ?
C2 C1 N1 120.96(16) . . ?
C6 C1 N1 119.14(15) . . ?
C6 C1 C2 119.90(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.85(17) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.57(17) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.34(17) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.48(18) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 117.98(15) . . ?
C5 C6 C1 118.63(16) . . ?
C5 C6 C7 123.12(16) . . ?
C6 C7 C15 107.61(14) . . ?
C8 C7 C6 107.67(13) . . ?
C8 C7 C14 112.68(15) . . ?
C8 C7 C15 107.14(14) . . ?
C14 C7 C6 113.21(15) . . ?
C14 C7 C15 108.24(14) . . ?
C9 C8 C7 123.56(16) . . ?
C9 C8 C13 117.86(16) . . ?
C13 C8 C7 118.29(15) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.88(18) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.11(16) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.65(17) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.05(17) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 N1 118.44(15) . . ?
C12 C13 N1 121.25(16) . . ?
C12 C13 C8 120.30(15) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N1 121.16(15) . . ?
C21 C16 N1 118.49(14) . . ?
C21 C16 C17 120.32(16) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.83(16) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.35(15) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 S1 119.63(13) . . ?
C18 C19 C20 121.06(16) . . ?
C20 C19 S1 119.31(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.34(16) . . ?
C21 C20 H20 120.3 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.07(15) . . ?
C20 C21 H21 120.0 . . ?
C23 C22 S1 121.06(14) . . ?
C23 C22 C27 120.48(18) . . ?
C27 C22 S1 118.41(14) . . ?
O1 C23 C22 124.37(17) . . ?
O1 C23 C24 117.12(17) . . ?
C24 C23 C22 118.49(18) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.44(19) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.7(2) . . ?
C27 C26 H26 120.2 . . ?
C22 C27 H27 120.1 . . ?
C26 C27 C22 119.74(19) . . ?
C26 C27 H27 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C19 C20 C21 178.01(13) . . . . ?
S1 C22 C23 O1 2.2(3) . . . . ?
S1 C22 C23 C24 -176.20(16) . . . . ?
S1 C22 C27 C26 176.44(18) . . . . ?
O1 C23 C24 C25 -178.8(2) . . . . ?
O2 S1 C19 C18 27.69(16) . . . . ?
O2 S1 C19 C20 -151.85(14) . . . . ?
O2 S1 C22 C23 -30.63(18) . . . . ?
O2 S1 C22 C27 151.86(15) . . . . ?
O3 S1 C19 C18 157.16(14) . . . . ?
O3 S1 C19 C20 -22.38(17) . . . . ?
O3 S1 C22 C23 -161.03(15) . . . . ?
O3 S1 C22 C27 21.46(18) . . . . ?
N1 C1 C2 C3 -178.83(15) . . . . ?
N1 C1 C6 C5 175.77(14) . . . . ?
N1 C1 C6 C7 -10.0(2) . . . . ?
N1 C16 C17 C18 176.32(15) . . . . ?
N1 C16 C21 C20 -176.32(15) . . . . ?
C1 N1 C13 C8 25.8(2) . . . . ?
C1 N1 C13 C12 -154.47(15) . . . . ?
C1 N1 C16 C17 77.5(2) . . . . ?
C1 N1 C16 C21 -104.31(18) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C1 C6 C7 C8 41.10(19) . . . . ?
C1 C6 C7 C14 166.34(15) . . . . ?
C1 C6 C7 C15 -74.10(18) . . . . ?
C2 C1 C6 C5 -5.3(2) . . . . ?
C2 C1 C6 C7 168.93(15) . . . . ?
C2 C3 C4 C5 -2.7(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 4.5(2) . . . . ?
C4 C5 C6 C7 -169.42(15) . . . . ?
C5 C6 C7 C8 -145.00(16) . . . . ?
C5 C6 C7 C14 -19.8(2) . . . . ?
C5 C6 C7 C15 99.81(18) . . . . ?
C6 C1 C2 C3 2.2(2) . . . . ?
C6 C7 C8 C9 145.28(17) . . . . ?
C6 C7 C8 C13 -41.0(2) . . . . ?
C7 C8 C9 C10 171.07(16) . . . . ?
C7 C8 C13 N1 10.0(2) . . . . ?
C7 C8 C13 C12 -169.80(15) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C8 C13 N1 -175.97(15) . . . . ?
C9 C8 C13 C12 4.3(2) . . . . ?
C9 C10 C11 C12 2.3(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 N1 177.56(16) . . . . ?
C11 C12 C13 C8 -2.7(3) . . . . ?
C13 N1 C1 C2 155.30(15) . . . . ?
C13 N1 C1 C6 -25.7(2) . . . . ?
C13 N1 C16 C17 -84.7(2) . . . . ?
C13 N1 C16 C21 93.51(18) . . . . ?
C13 C8 C9 C10 -2.6(3) . . . . ?
C14 C7 C8 C9 19.7(2) . . . . ?
C14 C7 C8 C13 -166.58(15) . . . . ?
C15 C7 C8 C9 -99.22(19) . . . . ?
C15 C7 C8 C13 74.48(18) . . . . ?
C16 N1 C1 C2 -6.8(2) . . . . ?
C16 N1 C1 C6 172.12(14) . . . . ?
C16 N1 C13 C8 -171.73(14) . . . . ?
C16 N1 C13 C12 8.0(2) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C16 C21 C20 1.9(3) . . . . ?
C17 C18 C19 S1 -177.96(13) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 S1 C22 C23 83.96(17) . . . . ?
C19 S1 C22 C27 -93.55(16) . . . . ?
C19 C20 C21 C16 -0.2(3) . . . . ?
C21 C16 C17 C18 -1.8(3) . . . . ?
C22 S1 C19 C18 -87.02(15) . . . . ?
C22 S1 C19 C20 93.44(15) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C22 C27 C26 -1.1(3) . . . . ?
C23 C24 C25 C26 -0.8(4) . . . . ?
C24 C25 C26 C27 1.0(4) . . . . ?
C25 C26 C27 C22 0.0(3) . . . . ?
C27 C22 C23 O1 179.64(19) . . . . ?
C27 C22 C23 C24 1.2(3) . . . . ?

_olex2_date_sample_data_collection 2019-01-17
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shanxi_4
_database_code_depnum_ccdc_archive 'CCDC 2472413'
loop_
_audit_author_name
_audit_author_address
'xiayan '
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2025-07-14 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 F N O2 S'
_chemical_formula_weight         443.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.17384(17)
_cell_length_b                   17.3356(4)
_cell_length_c                   15.9288(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.372(2)
_cell_angle_gamma                90
_cell_volume                     2195.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.583
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7812
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.826
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_full        66.598
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3770
_reflns_number_gt                3201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3770
_refine_ls_number_parameters     354
_refine_ls_number_restraints     84
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70310(6) 0.18970(4) 0.89945(4) 0.0612(2) Uani 1 1 d . . . . .
O1 O 0.5671(2) 0.21578(15) 0.93425(16) 0.1009(8) Uani 1 1 d . . . . .
O2 O 0.6956(2) 0.19986(12) 0.80967(11) 0.0827(6) Uani 1 1 d . . . . .
N1 N 1.32497(17) 0.34204(9) 1.09894(10) 0.0445(4) Uani 1 1 d . . . . .
C1 C 1.3129(2) 0.42128(11) 1.11746(12) 0.0432(4) Uani 1 1 d . . . . .
C2 C 1.1598(2) 0.45976(12) 1.10046(15) 0.0541(5) Uani 1 1 d . . . . .
H2 H 1.061971 0.433453 1.074498 0.065 Uiso 1 1 calc R U . . .
C3 C 1.1510(3) 0.53650(14) 1.12164(18) 0.0679(6) Uani 1 1 d . . . . .
H3 H 1.047769 0.561670 1.109778 0.081 Uiso 1 1 calc R U . . .
C4 C 1.2944(4) 0.57584(14) 1.1602(2) 0.0758(7) Uani 1 1 d . . . . .
H4 H 1.288630 0.627116 1.176394 0.091 Uiso 1 1 calc R U . . .
C5 C 1.4469(3) 0.53835(15) 1.17447(18) 0.0699(6) Uani 1 1 d . . . . .
H5 H 1.543771 0.565491 1.199950 0.084 Uiso 1 1 calc R U . . .
C6 C 1.4616(2) 0.46168(12) 1.15234(13) 0.0495(5) Uani 1 1 d . . . . .
C7 C 1.6289(2) 0.42155(13) 1.15503(15) 0.0545(5) Uani 1 1 d . . . . .
C8 C 1.6129(2) 0.33808(13) 1.18143(12) 0.0469(5) Uani 1 1 d . . . . .
C9 C 1.7435(3) 0.29615(16) 1.23272(14) 0.0605(6) Uani 1 1 d . . . . .
H9 H 1.842236 0.321542 1.259096 0.073 Uiso 1 1 calc R U . . .
C10 C 1.7307(3) 0.21810(18) 1.24556(16) 0.0701(7) Uani 1 1 d . . . . .
H10 H 1.820108 0.191290 1.279937 0.084 Uiso 1 1 calc R U . . .
C11 C 1.5857(3) 0.18014(15) 1.20748(18) 0.0720(7) Uani 1 1 d . . . . .
H11 H 1.578114 0.127065 1.214185 0.086 Uiso 1 1 calc R U . . .
C12 C 1.4499(3) 0.22069(13) 1.15886(16) 0.0601(6) Uani 1 1 d . . . . .
H12 H 1.350455 0.194915 1.134513 0.072 Uiso 1 1 calc R U . . .
C13 C 1.4620(2) 0.29954(11) 1.14648(12) 0.0441(4) Uani 1 1 d . . . . .
C14 C 1.7779(3) 0.4633(2) 1.2135(2) 0.0899(9) Uani 1 1 d . . . . .
H14A H 1.763153 0.464076 1.271530 0.135 Uiso 1 1 calc R U . . .
H14B H 1.783586 0.515184 1.193406 0.135 Uiso 1 1 calc R U . . .
H14C H 1.880189 0.436633 1.212071 0.135 Uiso 1 1 calc R U . . .
C15 C 1.6555(3) 0.42150(16) 1.06204(17) 0.0684(7) Uani 1 1 d . . . . .
H15A H 1.759712 0.396255 1.061332 0.103 Uiso 1 1 calc R U . . .
H15B H 1.658875 0.473694 1.042364 0.103 Uiso 1 1 calc R U . . .
H15C H 1.564465 0.394530 1.024695 0.103 Uiso 1 1 calc R U . . .
C16 C 1.1778(2) 0.30244(10) 1.05266(13) 0.0426(4) Uani 1 1 d . . . . .
C17 C 1.1624(2) 0.28601(13) 0.96651(14) 0.0510(5) Uani 1 1 d . . . . .
H17 H 1.249105 0.298726 0.940179 0.061 Uiso 1 1 calc R U . . .
C18 C 1.0182(3) 0.25059(13) 0.91875(13) 0.0536(5) Uani 1 1 d . . . . .
H18 H 1.007755 0.239099 0.860715 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8908(2) 0.23279(11) 0.95922(13) 0.0465(4) Uani 1 1 d . . . . .
C20 C 0.9061(2) 0.24718(13) 1.04612(14) 0.0524(5) Uani 1 1 d . . . . .
H20 H 0.820079 0.233597 1.072608 0.063 Uiso 1 1 calc R U . . .
C21 C 1.0512(2) 0.28211(12) 1.09334(13) 0.0500(5) Uani 1 1 d . . . . .
H21 H 1.063439 0.291836 1.151893 0.060 Uiso 1 1 calc R U . . .
F1 F 0.7343(9) -0.0473(3) 1.0875(3) 0.210(3) Uani 0.6 1 d . U P A 1
C22 C 0.7447(16) 0.0847(6) 0.9221(9) 0.050(2) Uani 0.6 1 d . U P A 1
C23 C 0.7254(10) 0.0562(5) 0.9972(6) 0.085(2) Uani 0.6 1 d . U P A 1
H23 H 0.687569 0.087296 1.036349 0.102 Uiso 0.6 1 calc R U P A 1
C24 C 0.7629(13) -0.0203(5) 1.0153(5) 0.100(2) Uani 0.6 1 d . U P A 1
C25 C 0.8195(11) -0.0657(5) 0.9600(6) 0.093(2) Uani 0.6 1 d . U P A 1
H25 H 0.843027 -0.117523 0.972102 0.111 Uiso 0.6 1 calc R U P A 1
C26 C 0.8419(13) -0.0327(6) 0.8841(6) 0.101(3) Uani 0.6 1 d . U P A 1
H26 H 0.879077 -0.063624 0.844499 0.121 Uiso 0.6 1 calc R U P A 1
C27 C 0.8116(15) 0.0428(10) 0.8657(7) 0.078(3) Uani 0.6 1 d . U P A 1
H27 H 0.835253 0.065193 0.816739 0.094 Uiso 0.6 1 calc R U P A 1
F1B F 0.9000(13) -0.0844(5) 0.8746(6) 0.182(3) Uani 0.4 1 d . U P A 2
C22B C 0.718(3) 0.1023(10) 0.9279(16) 0.058(4) Uani 0.4 1 d . U P A 2
C23B C 0.6577(13) 0.0753(7) 0.9983(8) 0.075(3) Uani 0.4 1 d . U P A 2
H23B H 0.605328 0.109626 1.028521 0.090 Uiso 0.4 1 calc R U P A 2
C24B C 0.6743(15) 0.0002(8) 1.0236(8) 0.101(3) Uani 0.4 1 d . U P A 2
H24B H 0.635770 -0.014954 1.071628 0.122 Uiso 0.4 1 calc R U P A 2
C25B C 0.746(2) -0.0538(10) 0.9808(11) 0.111(5) Uani 0.4 1 d . U P A 2
H25B H 0.754059 -0.104932 0.998858 0.134 Uiso 0.4 1 calc R U P A 2
C26B C 0.802(2) -0.0323(10) 0.9141(12) 0.103(4) Uani 0.4 1 d . U P A 2
C27B C 0.776(2) 0.0459(14) 0.8813(13) 0.080(5) Uani 0.4 1 d . U P A 2
H27B H 0.797981 0.058018 0.828148 0.096 Uiso 0.4 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.425(2) . ?
S1 O2 1.428(2) . ?
S1 C22B 1.58(2) . ?
S1 C19 1.7728(18) . ?
S1 C22 1.872(11) . ?
N1 C13 1.407(2) . ?
N1 C1 1.413(3) . ?
N1 C16 1.433(2) . ?
C1 C2 1.389(3) . ?
C1 C6 1.401(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.526(3) . ?
C7 C8 1.521(3) . ?
C7 C14 1.532(3) . ?
C7 C15 1.546(3) . ?
C8 C9 1.390(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.378(3) . ?
C16 C21 1.388(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(3) . ?
C20 C21 1.388(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
F1 C24 1.312(9) . ?
C22 C23 1.338(17) . ?
C22 C27 1.364(15) . ?
C23 C24 1.375(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.341(14) . ?
C25 C26 1.387(14) . ?
C25 H25 0.9300 . ?
C26 C27 1.352(19) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
F1B C26B 1.443(17) . ?
C22B C27B 1.38(2) . ?
C22B C23B 1.40(3) . ?
C23B C24B 1.360(19) . ?
C23B H23B 0.9300 . ?
C24B C25B 1.36(2) . ?
C24B H24B 0.9300 . ?
C25B C26B 1.31(2) . ?
C25B H25B 0.9300 . ?
C26B C27B 1.45(3) . ?
C27B H27B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.58(14) . . ?
O1 S1 C22B 101.9(8) . . ?
O2 S1 C22B 112.9(9) . . ?
O1 S1 C19 108.25(11) . . ?
O2 S1 C19 108.49(10) . . ?
C22B S1 C19 104.6(8) . . ?
O1 S1 C22 110.9(4) . . ?
O2 S1 C22 106.1(4) . . ?
C19 S1 C22 102.1(4) . . ?
C13 N1 C1 118.81(15) . . ?
C13 N1 C16 119.71(16) . . ?
C1 N1 C16 118.85(14) . . ?
C2 C1 C6 119.81(19) . . ?
C2 C1 N1 121.95(17) . . ?
C6 C1 N1 118.22(16) . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 122.6(2) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 117.49(19) . . ?
C5 C6 C7 124.00(19) . . ?
C1 C6 C7 118.20(18) . . ?
C8 C7 C6 107.92(16) . . ?
C8 C7 C14 112.8(2) . . ?
C6 C7 C14 112.5(2) . . ?
C8 C7 C15 107.73(19) . . ?
C6 C7 C15 107.29(18) . . ?
C14 C7 C15 108.3(2) . . ?
C9 C8 C13 118.0(2) . . ?
C9 C8 C7 123.84(19) . . ?
C13 C8 C7 117.92(16) . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 119.92(18) . . ?
C12 C13 N1 121.21(17) . . ?
C8 C13 N1 118.86(18) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 H15A 109.5 . . ?
C7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 120.41(17) . . ?
C17 C16 N1 118.94(17) . . ?
C21 C16 N1 120.64(17) . . ?
C16 C17 C18 120.48(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 118.61(19) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C18 C19 C20 121.57(17) . . ?
C18 C19 S1 119.73(15) . . ?
C20 C19 S1 118.69(15) . . ?
C19 C20 C21 119.29(18) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C21 C20 119.58(18) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C27 122.7(11) . . ?
C23 C22 S1 118.5(8) . . ?
C27 C22 S1 118.3(11) . . ?
C22 C23 C24 118.5(8) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
F1 C24 C25 121.7(9) . . ?
F1 C24 C23 116.8(9) . . ?
C25 C24 C23 121.5(8) . . ?
C24 C25 C26 117.8(8) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
C27 C26 C25 122.2(9) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C26 C27 C22 117.0(11) . . ?
C26 C27 H27 121.5 . . ?
C22 C27 H27 121.5 . . ?
C27B C22B C23B 114.9(18) . . ?
C27B C22B S1 123(2) . . ?
C23B C22B S1 122.2(13) . . ?
C24B C23B C22B 121.8(12) . . ?
C24B C23B H23B 119.1 . . ?
C22B C23B H23B 119.1 . . ?
C23B C24B C25B 122.2(14) . . ?
C23B C24B H24B 118.9 . . ?
C25B C24B H24B 118.9 . . ?
C26B C25B C24B 118.9(16) . . ?
C26B C25B H25B 120.6 . . ?
C24B C25B H25B 120.6 . . ?
C25B C26B F1B 120.8(17) . . ?
C25B C26B C27B 120.5(15) . . ?
F1B C26B C27B 118.7(14) . . ?
C22B C27B C26B 120.7(17) . . ?
C22B C27B H27B 119.6 . . ?
C26B C27B H27B 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 -154.53(19) . . . . ?
C16 N1 C1 C2 7.0(3) . . . . ?
C13 N1 C1 C6 26.8(3) . . . . ?
C16 N1 C1 C6 -171.63(18) . . . . ?
C6 C1 C2 C3 -3.4(3) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 -2.7(4) . . . . ?
C4 C5 C6 C7 170.8(2) . . . . ?
C2 C1 C6 C5 4.7(3) . . . . ?
N1 C1 C6 C5 -176.6(2) . . . . ?
C2 C1 C6 C7 -169.16(19) . . . . ?
N1 C1 C6 C7 9.5(3) . . . . ?
C5 C6 C7 C8 145.6(2) . . . . ?
C1 C6 C7 C8 -41.0(3) . . . . ?
C5 C6 C7 C14 20.5(3) . . . . ?
C1 C6 C7 C14 -166.1(2) . . . . ?
C5 C6 C7 C15 -98.5(3) . . . . ?
C1 C6 C7 C15 74.9(2) . . . . ?
C6 C7 C8 C9 -144.7(2) . . . . ?
C14 C7 C8 C9 -19.7(3) . . . . ?
C15 C7 C8 C9 99.8(2) . . . . ?
C6 C7 C8 C13 40.5(2) . . . . ?
C14 C7 C8 C13 165.5(2) . . . . ?
C15 C7 C8 C13 -75.0(2) . . . . ?
C13 C8 C9 C10 3.6(3) . . . . ?
C7 C8 C9 C10 -171.1(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 -2.5(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C11 C12 C13 C8 1.5(3) . . . . ?
C11 C12 C13 N1 -178.7(2) . . . . ?
C9 C8 C13 C12 -4.1(3) . . . . ?
C7 C8 C13 C12 170.9(2) . . . . ?
C9 C8 C13 N1 176.03(18) . . . . ?
C7 C8 C13 N1 -8.9(3) . . . . ?
C1 N1 C13 C12 152.9(2) . . . . ?
C16 N1 C13 C12 -8.5(3) . . . . ?
C1 N1 C13 C8 -27.3(3) . . . . ?
C16 N1 C13 C8 171.33(17) . . . . ?
C13 N1 C16 C17 -95.0(2) . . . . ?
C1 N1 C16 C17 103.6(2) . . . . ?
C13 N1 C16 C21 86.2(2) . . . . ?
C1 N1 C16 C21 -75.2(2) . . . . ?
C21 C16 C17 C18 1.6(3) . . . . ?
N1 C16 C17 C18 -177.29(19) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 -2.1(3) . . . . ?
C17 C18 C19 S1 178.48(17) . . . . ?
O1 S1 C19 C18 -147.5(2) . . . . ?
O2 S1 C19 C18 -16.3(2) . . . . ?
C22B S1 C19 C18 104.4(9) . . . . ?
C22 S1 C19 C18 95.4(5) . . . . ?
O1 S1 C19 C20 33.0(2) . . . . ?
O2 S1 C19 C20 164.19(18) . . . . ?
C22B S1 C19 C20 -75.1(9) . . . . ?
C22 S1 C19 C20 -84.1(5) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
S1 C19 C20 C21 -178.89(17) . . . . ?
C17 C16 C21 C20 -2.0(3) . . . . ?
N1 C16 C21 C20 176.85(18) . . . . ?
C19 C20 C21 C16 0.4(3) . . . . ?
O1 S1 C22 C23 -35.8(10) . . . . ?
O2 S1 C22 C23 -167.1(8) . . . . ?
C19 S1 C22 C23 79.3(9) . . . . ?
O1 S1 C22 C27 151.5(9) . . . . ?
O2 S1 C22 C27 20.2(11) . . . . ?
C19 S1 C22 C27 -93.3(10) . . . . ?
C27 C22 C23 C24 -5.0(17) . . . . ?
S1 C22 C23 C24 -177.3(8) . . . . ?
C22 C23 C24 F1 -176.6(9) . . . . ?
C22 C23 C24 C25 0.8(15) . . . . ?
F1 C24 C25 C26 178.3(9) . . . . ?
C23 C24 C25 C26 1.0(14) . . . . ?
C24 C25 C26 C27 1.2(15) . . . . ?
C25 C26 C27 C22 -5.0(17) . . . . ?
C23 C22 C27 C26 7.0(19) . . . . ?
S1 C22 C27 C26 179.3(9) . . . . ?
O1 S1 C22B C27B 151.0(18) . . . . ?
O2 S1 C22B C27B 21(2) . . . . ?
C19 S1 C22B C27B -96.3(19) . . . . ?
O1 S1 C22B C23B -23.1(18) . . . . ?
O2 S1 C22B C23B -152.6(14) . . . . ?
C19 S1 C22B C23B 89.6(17) . . . . ?
C27B C22B C23B C24B 7(2) . . . . ?
S1 C22B C23B C24B -178.4(12) . . . . ?
C22B C23B C24B C25B -2(2) . . . . ?
C23B C24B C25B C26B 1(2) . . . . ?
C24B C25B C26B F1B 171.0(12) . . . . ?
C24B C25B C26B C27B -6(3) . . . . ?
C23B C22B C27B C26B -12(3) . . . . ?
S1 C22B C27B C26B 173.9(15) . . . . ?
C25B C26B C27B C22B 11(3) . . . . ?
F1B C26B C27B C22B -165.2(17) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.041

